How to Send Recurring Invoices
Sending recurring invoices is the critical step between generating a bill and getting paid. This guide covers how to deliver recurring invoices effectively — from automatic email delivery to following up on unpaid invoices and optimizing for faster payment.
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Quick Answer
Send recurring invoices by setting up a recurring schedule in your invoicing software. The software automatically generates each invoice on the billing date and delivers it via email to your client. You can choose fully automatic delivery or review-before-send mode.
Definition
Sending recurring invoices is the process of automatically delivering generated invoices to clients via email on a predefined schedule, including the invoice document, payment instructions, and any applicable payment links.
Automatic vs Manual Delivery
Automatic delivery means the software sends each invoice immediately after generation — no action needed from you. Manual review mode generates the invoice but holds it for your approval before sending. Start with manual review for the first 2-3 cycles to verify accuracy, then switch to automatic delivery once you trust the setup.
Setting Up Email Delivery
Configure your sender name and email address in your invoicing software. Customize the email subject line (include the invoice number and billing period). Write a professional email body that includes a greeting, invoice summary, and payment instructions. Attach the invoice as a PDF and include a payment link if available.
Best Time to Send Recurring Invoices
Send invoices on the 1st or 15th of the month to align with client accounting cycles. Tuesday through Thursday mornings see the highest open rates for business emails. Avoid sending on Fridays or weekends when invoices get buried. For Net 15 terms, sending on the 1st gives clients until the 16th — well within a single accounting period.
Following Up on Unpaid Invoices
Set up a 3-stage reminder sequence: a friendly reminder 3 days before the due date, a direct notice on the due date, and a firmer follow-up 7 days after. Each reminder should include the invoice number, amount due, and a payment link. Automated reminders handle 80% of late payment situations without manual intervention.
Invoice Delivery Best Practices
Always include a PDF attachment — some clients need it for their accounting software. Include a one-click payment link for faster payment. State the amount due and due date clearly in the email body. Reference the billing period so clients know what the invoice covers. Keep the email professional but concise — save details for the invoice itself.
Troubleshooting Delivery Issues
If invoices are not being received, check the client email address for typos. Ask clients to check spam/junk folders and whitelist your sending address. Verify your invoicing software email delivery settings. Consider sending a test invoice to yourself first. If emails consistently bounce, request an alternative billing contact email.
Key Takeaway
Sending recurring invoices is best done automatically through invoicing software. Set up email delivery, enable payment reminders, and your invoices go out on schedule every billing cycle without manual effort.
Frequently Asked Questions
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Set up a recurring invoice in your invoicing software, configure the billing schedule and client email, and enable automatic delivery. The software sends each invoice on the billing date without manual action.
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The 1st or 15th of the month, Tuesday through Thursday mornings. This aligns with client accounting cycles and maximizes the chance your invoice is seen and paid promptly.
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Both. Attach the PDF for the client records and include a payment link for quick payment. This covers clients who need formal documents and those who prefer to pay immediately.
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Check the email address, ask them to check spam folders, and resend from your invoicing software. For persistent issues, request an alternative billing email or send a PDF directly.
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